FR3087442B1 - HYDROCARBON COPOLYMERS WITH ALTERNATE BLOCKS AND ALCOXYSILANE TERMINAL GROUPS - Google Patents

HYDROCARBON COPOLYMERS WITH ALTERNATE BLOCKS AND ALCOXYSILANE TERMINAL GROUPS Download PDF

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Publication number
FR3087442B1
FR3087442B1 FR1859622A FR1859622A FR3087442B1 FR 3087442 B1 FR3087442 B1 FR 3087442B1 FR 1859622 A FR1859622 A FR 1859622A FR 1859622 A FR1859622 A FR 1859622A FR 3087442 B1 FR3087442 B1 FR 3087442B1
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FR
France
Prior art keywords
radical
zero
groups
integer
alcoxysilane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
FR1859622A
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French (fr)
Other versions
FR3087442A1 (en
Inventor
Stephane Fouquay
Frederic Simon
Guillaume Michaud
Cyril Chauveau
Jean-Francois Carpentier
Sophie Guillaume
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Centre National de la Recherche Scientifique CNRS
Universite de Rennes 1
Bostik SA
Original Assignee
Centre National de la Recherche Scientifique CNRS
Universite de Rennes 1
Bostik SA
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Publication date
Application filed by Centre National de la Recherche Scientifique CNRS, Universite de Rennes 1, Bostik SA filed Critical Centre National de la Recherche Scientifique CNRS
Priority to FR1859622A priority Critical patent/FR3087442B1/en
Priority to PCT/FR2019/052458 priority patent/WO2020079370A1/en
Publication of FR3087442A1 publication Critical patent/FR3087442A1/en
Application granted granted Critical
Publication of FR3087442B1 publication Critical patent/FR3087442B1/en
Expired - Fee Related legal-status Critical Current
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09J201/10—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J165/00—Adhesives based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3323—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other monocyclic systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/418—Ring opening metathesis polymerisation [ROMP]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/419—Acyclic diene metathesis [ADMET]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/70—Post-treatment
    • C08G2261/72—Derivatisation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Silicon Polymers (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

1)Copolymère à blocs alternés de formule (I): dans laquelle : - F1 et F2 sont 2 groupements de type alcoxysilane ; - R1 à R12 représentent un atome d'hydrogène ou un radical alkyle comprenant de 1 à 22 atomes de carbone ; - A représente O ou le groupe NR14 où R14 est un atome d'hydrogène ou un radical alkyle comprenant de 1 à 20 atomes de carbone ; - X représente un radical divalent comprenant un radical polymérique divalent T qui est relié directement ou indirectement à A, ledit radical T comprenant lui-même au moins un radical polyéther ; - x et y sont des entiers allant de 0 à 6, la somme x + y étant comprise dans une fourchette allant de 0 à 6 ; n1 et n2 sont un nombre entier ou nul ; m est un entier supérieur ou égal à 0 ; p1 et p2 sont un nombre entier ou nul dont la somme p1 + p2 est non nulle 2) Procédé de préparation dudit copolymère à partir de cyclooctadiène, d'un polymère (B) à groupes terminaux diacrylate, et d'un agent de transfert de chaîne (G) comprenant 2 groupements alcoxysilane. 3) Composition adhésive comprenant ledit copolymère et de 0,01 à 3% en poids d'un catalyseur de réticulation.1) Alternating block copolymer of formula (I): in which: - F1 and F2 are 2 groups of alkoxysilane type; - R1 to R12 represent a hydrogen atom or an alkyl radical comprising from 1 to 22 carbon atoms; - A represents O or the group NR14 where R14 is a hydrogen atom or an alkyl radical comprising from 1 to 20 carbon atoms; - X represents a divalent radical comprising a divalent polymeric radical T which is directly or indirectly linked to A, said radical T itself comprising at least one polyether radical; - x and y are integers ranging from 0 to 6, the sum x + y being within a range ranging from 0 to 6; n1 and n2 are an integer or zero; m is an integer greater than or equal to 0; p1 and p2 are an integer or zero, the sum of which p1 + p2 is non-zero 2) Process for preparing said copolymer from cyclooctadiene, a polymer (B) containing diacrylate end groups, and a transfer agent chain (G) comprising 2 alkoxysilane groups. 3) Adhesive composition comprising said copolymer and from 0.01 to 3% by weight of a crosslinking catalyst.

FR1859622A 2018-10-18 2018-10-18 HYDROCARBON COPOLYMERS WITH ALTERNATE BLOCKS AND ALCOXYSILANE TERMINAL GROUPS Expired - Fee Related FR3087442B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FR1859622A FR3087442B1 (en) 2018-10-18 2018-10-18 HYDROCARBON COPOLYMERS WITH ALTERNATE BLOCKS AND ALCOXYSILANE TERMINAL GROUPS
PCT/FR2019/052458 WO2020079370A1 (en) 2018-10-18 2019-10-17 Hydrocarbon copolymers with alternating blocks and alkoxysilane end groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1859622A FR3087442B1 (en) 2018-10-18 2018-10-18 HYDROCARBON COPOLYMERS WITH ALTERNATE BLOCKS AND ALCOXYSILANE TERMINAL GROUPS

Publications (2)

Publication Number Publication Date
FR3087442A1 FR3087442A1 (en) 2020-04-24
FR3087442B1 true FR3087442B1 (en) 2020-10-02

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FR (1) FR3087442B1 (en)
WO (1) WO2020079370A1 (en)

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2593888A (en) 1945-10-16 1952-04-22 Gen Aniline & Film Corp Production of hydroxyalkyl amides of acrylic acids
DE3825637A1 (en) 1988-07-28 1990-03-08 Rwe Dea Ag SECONDARY POLYETHERAMINE, THEIR PRODUCTION AND USE THEREOF FOR THE PRODUCTION OF POLYHANE MATERIALS
US4994621A (en) 1989-04-17 1991-02-19 Texaco Chemical Company Aminated, alkoxylated hydroxyl-terminated polybutadienes
CA2019824A1 (en) 1989-06-28 1990-12-28 Seiji Arimatsu Polyether acrylamide derivatives and active energy ray curable resin composition
GB9111794D0 (en) 1991-05-31 1991-07-24 Robins David J Antifungal compounds
EP1251135A3 (en) 1992-04-03 2004-01-02 California Institute Of Technology High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof
US5362913A (en) 1992-11-16 1994-11-08 Huntsman Corporation Saturated, aminated, alkoxylated polybutadienes
US6464850B1 (en) 1998-07-31 2002-10-15 Biowhittaker Molecular Applications, Inc. Method for producing hydrophilic monomers and uses thereof
US6175037B1 (en) 1998-10-09 2001-01-16 Ucb, S.A. Process for the preparation of (meth)acrylate esters and polyester (meth)acrylates using microwave energy as a heating source
GB9916235D0 (en) 1999-07-09 1999-09-15 Univ Durham Process for polymerisation of olefins and novel polymerisable olefins
US6943213B2 (en) 2003-08-13 2005-09-13 Acushnet Company Polyalkylacrylate compounds for use in golf balls
WO2001083097A2 (en) 2000-05-04 2001-11-08 University Of Florida Metathesis of functionalized allylic olefins
DE10101387A1 (en) 2001-01-13 2002-07-18 Merck Patent Gmbh Polyester with methacrylate end groups
DE10228540A1 (en) 2002-06-26 2004-01-22 Ivoclar Vivadent Ag Dental materials based on hydroxyalkylacrylamides
CN101253206A (en) 2005-09-02 2008-08-27 三井化学聚氨酯株式会社 Meth) acylate-grafted polyether polyol, and process for production and use thereof
JP5153653B2 (en) 2006-02-09 2013-02-27 クレイ・バレー・テクノロジー・ユーエスエイ・リミテッド・ライアビリティ・カンパニー Polybutadiene compositions, methods and articles
US8283410B2 (en) 2009-03-30 2012-10-09 Isp Investments Inc. Ring-opening metathesis polymerization of norbornene and oxanorbornene moieties and uses thereof
JP6025476B2 (en) 2012-09-21 2016-11-16 昭和電工株式会社 Process for producing ethylenically unsaturated group-containing isocyanate compound
FR2997957B1 (en) 2012-11-12 2015-01-16 Bostik Sa RENEWABLE BICOMPONENT LAMINATION ADHESIVE
EP2886578A1 (en) 2013-12-20 2015-06-24 Nitto Denko Corporation Hydrophilic skin adhesive
FR3051471A1 (en) * 2016-05-17 2017-11-24 Bostik Sa HYDROCARBON POLYMERS WITH TWO ALCOXYSILANE TERMINAL GROUPS
WO2018002473A1 (en) 2016-06-29 2018-01-04 Bostik Sa New hydrocarbon polymers comprising two alkoxysilane end groups, and methods for preparing same

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Publication number Publication date
FR3087442A1 (en) 2020-04-24
WO2020079370A1 (en) 2020-04-23

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